Abstract:
:We have obtained the optimized geometrical structure of 2-(1-carboxy-1-hydroxyethyl)-3,4-dimethylthiazolium dipolar ion and investigated its geometric and electric changes during decarboxylation process by the MNDO-PM3 method, a molecular orbital method. The salient features of the optimized structure are that the dihedral angle of C4-C1-C2-S3 is 5.4 degrees and the distance between thiazolium S3 and carboxyl O6 is about 1.8 A (the bond order between S3 and O6 is about 0.4). The lowest energy decarboxylation profile is the following process. First the dihedral angle of C4-C1-C2-S3 becomes about 90 degrees, then the distance between C1-C2 increases while the dihedral angle holds about 90 degrees, and finally the C1-C2 bond disappears. The most remarkable change caused by the 90 degrees rotation is the disappearance of the S3-O6 bond, and this disappearance causes electric changes that prompt the decarboxylation.
journal_name
Biochem Biophys Res Communjournal_title
Biochemical and biophysical research communicationsauthors
Nakajima Y,Sakagishi Y,Shiibashi M,Suzuki Y,Kato Hdoi
10.1006/bbrc.1993.2064subject
Has Abstractpub_date
1993-08-31 00:00:00pages
449-54issue
1eissn
0006-291Xissn
1090-2104pii
S0006291X83720644journal_volume
195pub_type
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